JP7450028B2 - ニコチンアミド化合物及び該化合物を含む除草剤組成物 - Google Patents
ニコチンアミド化合物及び該化合物を含む除草剤組成物 Download PDFInfo
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- JP7450028B2 JP7450028B2 JP2022523365A JP2022523365A JP7450028B2 JP 7450028 B2 JP7450028 B2 JP 7450028B2 JP 2022523365 A JP2022523365 A JP 2022523365A JP 2022523365 A JP2022523365 A JP 2022523365A JP 7450028 B2 JP7450028 B2 JP 7450028B2
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- Prior art keywords
- methyl
- tetrazol
- trifluoromethyl
- nicotinamide
- group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 537
- -1 Nicotinamide compound Chemical class 0.000 title claims description 329
- 239000000203 mixture Substances 0.000 title claims description 224
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims description 197
- 235000005152 nicotinamide Nutrition 0.000 title claims description 111
- 239000011570 nicotinamide Substances 0.000 title claims description 111
- 229960003966 nicotinamide Drugs 0.000 title claims description 111
- 230000002363 herbicidal effect Effects 0.000 title claims description 56
- 239000004009 herbicide Substances 0.000 title claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 249
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 122
- 238000003786 synthesis reaction Methods 0.000 claims description 104
- 230000015572 biosynthetic process Effects 0.000 claims description 101
- 239000000126 substance Substances 0.000 claims description 93
- 241000196324 Embryophyta Species 0.000 claims description 75
- 239000003112 inhibitor Substances 0.000 claims description 67
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 58
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 42
- 235000001968 nicotinic acid Nutrition 0.000 claims description 38
- 239000011664 nicotinic acid Substances 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 19
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- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
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- 150000002431 hydrogen Chemical class 0.000 claims description 14
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- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 13
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- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 12
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
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- 230000000996 additive effect Effects 0.000 claims description 11
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- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 10
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- 238000000034 method Methods 0.000 claims description 10
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
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- 239000000460 chlorine Substances 0.000 claims description 7
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
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- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims description 5
- 229930192334 Auxin Natural products 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000002363 auxin Substances 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
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- 108010060806 Photosystem II Protein Complex Proteins 0.000 claims description 4
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims description 4
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims description 4
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
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- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- HNERGUZACGVRGO-UHFFFAOYSA-N trifluoromethyl pyridine-3-carboxylate Chemical compound FC(F)(F)OC(=O)C1=CC=CN=C1 HNERGUZACGVRGO-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
- A01P13/02—Herbicides; Algicides selective
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2019-0130935 | 2019-10-21 | ||
KR20190130935 | 2019-10-21 | ||
PCT/KR2020/014438 WO2021080330A1 (ko) | 2019-10-21 | 2020-10-21 | 니코틴아마이드 화합물 및 이 화합물을 포함하는 제초제 조성물 |
Publications (2)
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JP2022552740A JP2022552740A (ja) | 2022-12-19 |
JP7450028B2 true JP7450028B2 (ja) | 2024-03-14 |
Family
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JP2022523365A Active JP7450028B2 (ja) | 2019-10-21 | 2020-10-21 | ニコチンアミド化合物及び該化合物を含む除草剤組成物 |
Country Status (15)
Country | Link |
---|---|
US (1) | US20220386607A1 (es) |
EP (1) | EP4050007A4 (es) |
JP (1) | JP7450028B2 (es) |
KR (1) | KR102632628B1 (es) |
CN (1) | CN114599644B (es) |
AR (1) | AR120266A1 (es) |
AU (1) | AU2020371005B2 (es) |
BR (1) | BR112022007456A2 (es) |
CA (1) | CA3154874C (es) |
CL (1) | CL2022000987A1 (es) |
MX (1) | MX2022004651A (es) |
TW (1) | TW202128652A (es) |
UA (1) | UA127915C2 (es) |
UY (1) | UY38929A (es) |
WO (1) | WO2021080330A1 (es) |
Families Citing this family (2)
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KR20220087222A (ko) * | 2020-12-17 | 2022-06-24 | 주식회사 팜한농 | N-(1-메틸-1h-테트라졸-5-일)-2-(((2-메틸-2h-테트라졸-5-일)메톡시)메틸)-6-(트리플루오로메틸)니코틴아마이드의 제조 방법 |
CN114957217A (zh) * | 2022-06-10 | 2022-08-30 | 华中师范大学 | 含有2-三氟甲基吡啶酰胺结构的化合物及其制备方法和应用、除草剂及其应用 |
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JP2015501325A (ja) | 2011-11-03 | 2015-01-15 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 5−フェニル置換n−(テトラゾール−5−イル)アリールカルボン酸アミドおよびn−(トリアゾール−5−イル)アリールカルボン酸アミド、ならびに除草剤としてのそれらの使用 |
JP2015505849A (ja) | 2011-12-13 | 2015-02-26 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | N−(1,2,5−オキサジアゾール−3−イル)−、n−(1,3,4−オキサジアゾール−2−イル)−、n−(テトラゾール−5−イル)−、およびn−(トリアゾール−5−イル)アリールカルボン酸アミド類ならびにそれらの除草剤としての使用 |
JP2015517456A (ja) | 2012-05-03 | 2015-06-22 | バイエル・クロップサイエンス・アーゲーBayer Cropscience Ag | N−(テトラゾール−5−イル)−およびn−(トリアゾール−5−イル)アリールカルボキサミド塩およびそれの除草剤としての使用 |
JP2015518847A (ja) | 2012-05-24 | 2015-07-06 | バイエル・クロップサイエンス・アーゲーBayer Cropscience Ag | N−(テトラゾール−5−イル)−およびn−(トリアゾール−5−イル)アリールカルボン酸チオアミド類ならびに除草剤としてのそれらの使用 |
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JP3462247B2 (ja) * | 1993-12-17 | 2003-11-05 | クミアイ化学工業株式会社 | カルボヒドロキシモイルアゾール誘導体及び殺虫剤 |
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WO2011125317A1 (ja) * | 2010-04-02 | 2011-10-13 | クミアイ化学工業株式会社 | トリアゾール誘導体及び有害生物防除剤 |
AU2011298424B2 (en) | 2010-09-01 | 2015-05-21 | Bayer Cropscience Aktiengesellschaft | N-(Tetrazol-5-yl)- and N-(Triazol-5-yl)arylcarboxamides and use thereof as herbicides |
PL2793589T3 (pl) * | 2011-12-21 | 2018-05-30 | Syngenta Limited | Związki herbicydowe |
WO2014175621A1 (en) * | 2013-04-25 | 2014-10-30 | Yuhan Corporation | Novel triazolone derivatives or salts thereof and pharmaceutical composition comprising the same |
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-
2020
- 2020-10-21 WO PCT/KR2020/014438 patent/WO2021080330A1/ko unknown
- 2020-10-21 US US17/770,681 patent/US20220386607A1/en active Pending
- 2020-10-21 KR KR1020200137051A patent/KR102632628B1/ko active IP Right Grant
- 2020-10-21 UA UAA202201643A patent/UA127915C2/uk unknown
- 2020-10-21 TW TW109136388A patent/TW202128652A/zh unknown
- 2020-10-21 BR BR112022007456A patent/BR112022007456A2/pt unknown
- 2020-10-21 CA CA3154874A patent/CA3154874C/en active Active
- 2020-10-21 AU AU2020371005A patent/AU2020371005B2/en active Active
- 2020-10-21 JP JP2022523365A patent/JP7450028B2/ja active Active
- 2020-10-21 UY UY0001038929A patent/UY38929A/es unknown
- 2020-10-21 MX MX2022004651A patent/MX2022004651A/es unknown
- 2020-10-21 EP EP20878665.7A patent/EP4050007A4/en active Pending
- 2020-10-21 CN CN202080073957.2A patent/CN114599644B/zh active Active
- 2020-10-21 AR ARP200102905A patent/AR120266A1/es unknown
-
2022
- 2022-04-20 CL CL2022000987A patent/CL2022000987A1/es unknown
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JP2015501325A (ja) | 2011-11-03 | 2015-01-15 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 5−フェニル置換n−(テトラゾール−5−イル)アリールカルボン酸アミドおよびn−(トリアゾール−5−イル)アリールカルボン酸アミド、ならびに除草剤としてのそれらの使用 |
JP2015505849A (ja) | 2011-12-13 | 2015-02-26 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | N−(1,2,5−オキサジアゾール−3−イル)−、n−(1,3,4−オキサジアゾール−2−イル)−、n−(テトラゾール−5−イル)−、およびn−(トリアゾール−5−イル)アリールカルボン酸アミド類ならびにそれらの除草剤としての使用 |
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JP2015518847A (ja) | 2012-05-24 | 2015-07-06 | バイエル・クロップサイエンス・アーゲーBayer Cropscience Ag | N−(テトラゾール−5−イル)−およびn−(トリアゾール−5−イル)アリールカルボン酸チオアミド類ならびに除草剤としてのそれらの使用 |
Also Published As
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---|---|
UA127915C2 (uk) | 2024-02-07 |
CA3154874A1 (en) | 2021-04-29 |
EP4050007A4 (en) | 2023-09-27 |
WO2021080330A1 (ko) | 2021-04-29 |
AU2020371005B2 (en) | 2024-02-22 |
KR20210047264A (ko) | 2021-04-29 |
AR120266A1 (es) | 2022-02-09 |
CL2022000987A1 (es) | 2023-01-13 |
CN114599644A (zh) | 2022-06-07 |
AU2020371005A1 (en) | 2022-05-26 |
JP2022552740A (ja) | 2022-12-19 |
UY38929A (es) | 2021-05-31 |
TW202128652A (zh) | 2021-08-01 |
BR112022007456A2 (pt) | 2022-07-12 |
US20220386607A1 (en) | 2022-12-08 |
MX2022004651A (es) | 2022-05-25 |
EP4050007A1 (en) | 2022-08-31 |
CA3154874C (en) | 2024-06-04 |
KR102632628B1 (ko) | 2024-02-01 |
CN114599644B (zh) | 2024-08-02 |
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